When asked why so many of Bart’s former lady loves were coming back at once, consulting producer Tim Long tells the publication, “It was a way to acknowledge that for a 10-year-old boy, Bart has gotten a lot of action. We thought it might be fun to borrow/pay homage to/steal an idea from ‘High Fidelity’ and have him go on a romantic pilgrimage and visit the girls that he dated and try to figure out how the hell he screwed things up with each of them…He realizes that maybe there’s something wrong with him after all.”

The premise of the episode is that Cletus’ daughter Mary (Deschanel) moves to New York. And Bart, thinking that she’s “the one,” decides to go find her.